Citation: Yang Jun, Fu Ting, Long Yang, Zhou Xiangge. Progress in Catalytic C-H Activation Reactions in Water[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1111-1116. doi: 10.6023/cjoc201702045 shu

Progress in Catalytic C-H Activation Reactions in Water

College of Chemistry, Sichuan University, Chengdu 610064

Corresponding author: Zhou Xiangge, zhouxiangge@scu.edu.cn
Received Date: 27 February 2017
Revised Date: 22 March 2017

Fund Project: the National Natural Science Foundation of China J1310008the National Natural Science Foundation of China Nos. 21472128

Figures(4)

C-H bond functionalization is one of the hot spots in the research field of organic chemistry, and selective C-H activation is a challenging project. Among these reactions, organic solvent is normally used as reaction media. Using cheap, environmentally friendly water as reaction solvent would be in line with the requirements of "green chemistry" and low-carbon sustainable development. This paper reviews the recent progress of aqueous catalyzed C-H functionalization reactions, including hybridized sp-, sp²-, and sp³-C-H bonds.
- catalysis,
- C-H activation,
- water,
- green chemistry
1. [1]
  Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283 (in Chinese).
2. [2]
  Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese).
3. [3]
  Hull, K.; Sanford, M. J. Am. Chem. Soc. 2007, 129, 11904.
4. [4]
  Desai, L.; Stowers, K.; Sanford, M. J. Am. Chem. Soc. 2008, 130, 13285.
5. [5]
  Joo, J.; Guo, P.; Sames, D. J. Org. Chem. 2013, 78, 738.
6. [6]
  Tan, J.; Chen, Y.; Li, H.; Yasuda, N. J. Org. Chem. 2014, 79, 8871.
7. [7]
  Batchu, H.; Bhattacharyya, S.; Kant, R.; Batra, S. J. Org. Chem. 2015, 80, 7360.
8. [8]
  Brahim, M.; Smari, I.; Ammar, H.; Hassine, B.; Soulé, J.; Doucet, H. Org. Chem. Front. 2015, 2, 917.
9. [9]
  Testa, C.; Roger, J.; Scheib, S.; Fleurat-Lessard, P.; Hierso, J. Adv. Synth. Catal. 2015, 357, 2913.
10. [10]
  Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094.
11. [11]
  Kim, M.; Kwak, J.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 8935.
12. [12]
  Gong, T.; Xiao, B.; Cheng, W.; Su, W.; Xu, J.; Liu, Z.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 10630.
13. [13]
  Reddy, V.; Qiu, R.; Iwasaki, T.; Kambe, N. Org. Lett. 2013, 15, 1290.
14. [14]
  Wang, H.; Schrçder, N.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 5386.
15. [15]
  Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780.
16. [16]
  Zhang, P.; Hong, L.; Li, G.; Wang, R. Adv. Synth. Catal. 2015, 357, 345.
17. [17]
  Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433.
18. [18]
  Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619.
19. [19]
  Oi, S.; Sasamoto, H.; Funayama, R.; Inoue, Y. Chem. Lett. 2008, 37, 994.
20. [20]
  Kumar, P.; Jeyachandran, R.; Ackermann, L. J. Org. Chem. 2013, 78, 4145.
21. [21]
  Ackermann, L.; Vicente, R.; Potukuchi, H.; Pirovano, V. Org. Lett. 2010, 12, 5032.
22. [22]
  Arockiam, P.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. Green Chem. 2011, 13, 3075.
23. [23]
  Muralirajan, K.; Parthasarathy, K.; Cheng, C. Org. Lett. 2012, 14, 4262.
24. [24]
  Hashimoto, Y.; Hirano, K.; Satoh, T.; Kakiuchi, F.; Miura, M. J. Org. Chem. 2013, 78, 638.
25. [25]
  Schinkel, M.; Marek, I.; Ackermann, L. Angew. Chem., Int. Ed. 2013, 52, 3977.
26. [26]
  Gonell, S.; Peris, E. ACS Catal. 2014, 4, 2811.
27. [27]
  Wei, C.; Li, C. J. Am. Chem. Soc. 2002, 124, 5638.
28. [28]
  Wei, C.; Li, C. J. Am. Chem. Soc. 2003, 125, 9584.
29. [29]
  Yao, X.; Li, C. Org. Lett. 2005, 7, 4395.
30. [30]
  Yao, X.; Li, C. Org. Lett. 2006, 8, 1953.
31. [31]
  Arockiam, P.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. Angew. Chem., Int. Ed. 2010, 49, 6629.
32. [32]
  Ackermann, L.; Lygin, A. Org. Lett. 2012, 14, 764.
33. [33]
  Ackermann, L.; Pospech, J.; Potukuchi, H. Org. Lett. 2012, 14, 2146.
34. [34]
  Wu, Z. Luo, F.; Chen, S.; Li, Z.; Xiang, H.; Zhou, X. Chem. Commun. 2013, 49, 7653.
35. [35]
  Wu, Z.; Chen, S.; Hu, C.; Li, Z.; Xiang, H.; Zhou, X. ChemCatChem 2013, 5, 2839.
36. [36]
  Lu, M.; Lu, P.; Xu, Y.; Loh, T. Org. Lett. 2014, 16, 2614.
37. [37]
  Luo, F.; Yang, J.; Li, Z.; Xiang, H.; Zhou, X. Eur. J. Org. Chem. 2015, 2463.
38. [38]
  Sun, S.; Shang, M.; Wang, H.; Lin, H.; Dai, H.; Yu, J. J. Org. Chem. 2015, 80, 8843.
39. [39]
  Gong, H.; Zeng, H.; Zhou, F.; Li, C. Angew. Chem., Int. Ed. 2015, 54, 5718.
40. [40]
  Xiao, F.; Chen, S.; Huang, H. Deng, G. Eur. J. Org. Chem. 2015, 7919.
41. [41]
  Ohnmacht, S.; Mamone, P.; Culshaw, A. Greaney, M. Chem. Commun. 2008, 1241.
42. [42]
  Ohnmacht, S.; Culshaw, A.; Greaney, M. Org. Lett. 2010, 12, 224.
43. [43]
  Ramirez, N.; Bosque, I.; Gonzalez-Gomez, J. Org. Lett. 2015, 17, 4550.
44. [44]
  Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2016, 18, 4144.
45. [45]
  Xiao, F.; Chen, S.; Tian, J.; Huang, H.; Liu, Y.; Deng, G. Green Chem. 2016, 18, 1538.
46. [46]
  Arumugam, V.; Kaminsky, W.; Nallasamy, D. Green Chem. 2016, 18, 3295.
47. [47]
  Hu, J.; Lan, T.; Sun, Y.; Chen, H.; Yao, J.; Rao, Y. Chem. Commun. 2015, 51, 14929.
48. [48]
  Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805 (in Chinese).
49. [49]
  Dohi, T.; Takenaga, N.; Goto, A.; Fujioka, H.; Kita, Y. J. Org. Chem. 2008, 73, 7365.
50. [50]
  Yi, C.; Kwon, K.; Lee, D. Org. Lett. 2009, 11, 1567.
51. [51]
  Pierce, C.; Hilinski, M. Org. Lett. 2014, 16, 6504.
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